The Anti-Pickup Artist

by David Wraith

David Wraith: The Anti-Tucker Max

I used to jokingly refer to myself as an “anti-pickup artist.” In my 20s this was meant to symbolize my abject failure with women. I made a fool out of myself chasing women who had no interest in me (to stalkerish proportions), I was clueless about how to flirt and oblivious to women who were flirting with me.

Now I’m looked at as someone who is “successful with women.” It’s hard to utter that phrase without sounding slightly douchey, but recognize that I don’t define success as the ability to get laid (although my multi-partner sex life is a product of my “success,” such that it is) but rather an ability to connect and engage with women socially and interpersonally. I still consider myself an “anti-pickup artist” but now it’s because my approach to women is a bit more Zen than the guys peacocking on Washington Avenue with a set of Tarot cards in their pocket.

Now that I’m being asked for my advice on how men should approach women, it’s made me have to actually sit down and think about my approach. Not because it comes naturally, but because it’s been a very slow evolution over a decade or so. So here’s some of what I’ve come up with.

A word about pickup lines: I think at this point in our cultural evolution, the myth of the pickup line is finally being put out to pasture. That magical combination of words that will make women from all different backgrounds weak in the knees, is now being kept in a vault between the fountain of youth and that machine that turns lead into gold. It’s guarded by the guys who only read Playboy for the articles.

Look, you’re a unique individual and so is the woman you’re hitting on. Saying something that any man could say to any woman shortchanges both of you. If a woman gets the impression that you’re using a line on her that you’ve used on a dozen other women, or that she’s heard from a dozen other men, she probably won’t be impressed. The best “pickup lines,” or compliments or openers, are the ones that arise organically out of the situation, are uniquely from you and specific to her. These are not transferable. Be original and more importantly, be sincere.

Give her fifty feet: As Kenny Rogers will tell you, part of being a Gambler is knowing when to fold ‘em and knowing when to walk away.  And Kenny knows that there’s a difference between the two. Walking away from a woman is not the same as giving up, it’s also not the same as being rude or getting your feelings hurt and walking away in a huff. Sometimes, politely excusing yourself from a conversation with the woman you’re attracted to is your best move. I know it sounds counterintuitive, but it’s Zen, remember?

It shows you’re not desperate. When you walk away before things get awkward, it communicates that you have things to do and other people to talk to. Guys who wear out their welcome give off an air of desperation, and that’s a huge turn off. If a woman thinks she can’t get rid of you, her mission will become getting rid of you.

It’s respectful of her time and privacy. Even if a woman is into you, it doesn’t mean she doesn’t want to mingle and talk to other people. Just because a woman wants to talk to other people, doesn’t mean she’s not interested in you. If the woman you’re hitting on gets involved in a personal conversation with someone else or gets a cell phone call that looks like it may be a minute, a wave, a gentle hand on the shoulder and a whispered “I’ll talk to you later,” is a great way to show that you respect her space and you’re not a hoverer.

It gives her a chance to chase you. Sometimes you will misjudge when a conversation has run its course and try to excuse yourself, only to have the woman you’re talking to grab you by the wrist and say, “Hey, where are you going?” or “What’s your rush?” This can only mean one of two things: either she wants to spend more time with you, or you are the only thing obscuring the view of the assassin who’s been sent to kill her. It’s probably the former and that’s a good sign.

Above all, don’t be “That Guy.” Or as Conan the Barbarian might say, “Hear the lamentation of the women.” When your single, female friends complain about the lousy ways guys try to approach them, pay attention. They’re telling you how not to be “That Guy.” Take it from a brother who spent a good portion of the 90s being that guy; you don’t want to be him.

No one is more surprised that I’m in this situation than I am, but I’ll be leading the workshop “Sex Positive Etiquette (for Men)” along with my friends Matthew and Justin. The workshop is for men only and will be held at Shameless Grounds on September 22^nd at 7pm.